Building an Organic Zeolite from a Macrocyclic TADDOL Derivative or How to Teach an Old Dog New Tricks

Crystal structures of the macrocyclic TADDOL (α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5-dimethanol) derivative A and its clathrate with diethyl ether are presented. Both the host and clathrate crystallize in the same space group (P212121) with very similar cell dimensions, i.e., they are isomorphous. At ambient temperature, diethyl ether escapes from A⋅Et2O, and clathrate single crystals are transformed into the guest-free form without breakdown of the crystal lattice. Conversely, crystalline A, when exposed to Et2O vapor, incorporates guest molecules in a ratio of up to ca. 1 : 1. This behavior, usually the hallmark of inorganic nanoporous materials, allows to describe this compound as an ‘organic zeolite'.